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Issue 28, 2016
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Synthesis of cyclopenta-fused polycyclic aromatic hydrocarbons utilizing aryl-substituted anilines

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Abstract

Cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs), potentially electronically and biologically highly active materials, were synthesized from readily available 2-aryl-substituted anilines. Reactions occur under extremely mild, room temperature conditions using tBuONO as the sole reagent. The use of a nitrite source generates a reactive diazonium intermediate in situ that then reacts with a tethered polycyclic aromatic moiety by intramolecular aromatic substitution. This protocol could be presented as one of the simplest methods to access CP-PAHs.

Graphical abstract: Synthesis of cyclopenta-fused polycyclic aromatic hydrocarbons utilizing aryl-substituted anilines

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Publication details

The article was received on 07 Jun 2016, accepted on 14 Jun 2016 and first published on 14 Jun 2016


Article type: Paper
DOI: 10.1039/C6OB01235C
Citation: Org. Biomol. Chem., 2016,14, 6804-6810
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    Synthesis of cyclopenta-fused polycyclic aromatic hydrocarbons utilizing aryl-substituted anilines

    Y. Choi, T. Chatterjee, J. Kim, J. S. Kim and E. J. Cho, Org. Biomol. Chem., 2016, 14, 6804
    DOI: 10.1039/C6OB01235C

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